Chicago to San Juan flights
The cheapest round trip we found from Chicago to San Juan is $204 (Jan 20 – 27, 2027, 1 stop), 8% below the usual $222.
CHI to SJU · Round trip · Economy · Prices per person in USD · Price found (1 day ago)
Cheapest found
Cheapest round trip by month
Lowest fare found per departure month| Month | Cheapest round trip |
|---|---|
| November 2026 | $267 |
| December 2026 | $222 |
| January 2027 | $204 (cheapest month) |
| February 2027 | No fares found yet |
| March 2027 | $342 |
Cheapest dates in the next 4 months
Round trip, per person-
Jan 20 – 27, 2027 7 nights · leave Wed$204 −8% vs usual$204 −8% vs usual Book
Frontier Airlines 1 stop · 5h 46m -
Nov 16 – 24 8 nights · leave Mon$267 +20% vs usual$267 +20% vs usual Book
Frontier Airlines 1 stop · 5h 50m
-
Nov 25 – Dec 2 7 nights · leave Wed$278 +25% vs usual$278 +25% vs usual Book
Frontier Airlines 1 stop · 4h 39m
-
Nov 23 – 29 6 nights · leave Mon$497 +124% vs usual$497 +124% vs usual Book
Frontier Airlines 1 stop · 5h 58m
Prices change often. The booking site shows the final price before you pay. Other dates? Set an alert
Plan the rest of your trip
San Juan · Jan 20 – 27, 2027- Car rental Economybookings · compare rental companies (opens Economybookings in a new tab)
- Things to do in San Juan Klook · tours and tickets (opens Klook in a new tab)
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Good to know
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Chicago to San Juan: questions
How much does a flight from Chicago to San Juan cost?
The cheapest round trip we have found right now is $204, leaving January 20 and returning January 27. The usual price on this route is about $222, so this fare is 8% less. Prices are per person, economy, in USD.
What is the cheapest month to fly from Chicago to San Juan?
January 2027, with round trips from $204. The most expensive month in our data is March (from $342). Based on the 4 months ahead we have prices for.
Which airports do Chicago to San Juan flights use?
Chicago airports include O'Hare International (ORD), Chicago Midway International (MDW) and Chicago Rockford International (RFD). San Juan airports include Luis Munoz Marin International (SJU) and Isla Grande (SIG). The prices on this page cover every airport in both cities (CHI and SJU are the city codes).
About this route
We track round-trip economy fares from Chicago (United States) to San Juan (Puerto Rico) using Travelpayouts / Aviasales data. The cheapest round trip we've found is $204, departing January 20 and returning January 27, about 8% below the usual $222. The cheapest month to fly in our data is January, from $204. Prices are per person and were correct when found; the final price is set by the airline or booking site when you book.